51 Chestnut Street Boston — Photo 1 of 40
$2,500,000
Investment Analysis — 51 Chestnut Street
Boston, MA 02129 — Charlestown
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 4-bedroom in 02129 carries an estimated $5,320/mo in gross rent — about a 0.71% cap rate and $17,790/yr in estimated NOI at the $2,500,000 list price. Adjust every assumption in the calculator below.
Beds
4
Baths
3.5
SqFt
3,593
Style
Single Family
Built
1865
Located on a gas-lit street near Monument Square, this rarely available, 4BR/3.5BA, two-family home offers 3,593+sf and an extraordinary opportunity for an owner occupant to live in the "owner's unit" and keep a tenant in 1st floor unit; or buyers looking to convert into a spectacular single family home; or a developer/investor to convert into two high-end condos. The grand entrance is defined by soaring ceilings, period moldings, and a sweeping staircase that leads to an impressive formal living room. An elegant dining room flows into a chef’s kitchen with luxury finishes and top-tier appliances. A charming family room w/wet bar and gas FP provides an inviting hub for daily living. A spacious primary suite w/fireplace has ample closet space and marble spa bath. An addt’l bedroom and full bath complete this level. The separate entrance, 1BR rental unit in the rear of the first floor is well maintained. The crown jewel is an expansive 480sf private roof deck w/head house, wet bar, and panoramic views of the harbor, Monument, and Boston skyline. An unfinished basement offers future expansion capabilities, and a lush garden patio completes this special offering.
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 3,593 sq ft principal dwelling). Lot size: 2,136 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Gas Water Heater • Water Heater • Tankless Water Heater • Range • Dishwasher • Disposal • Microwave • Refrigerator • Freezer • Washer • Dryer • Range Hood • Stainless Steel Appliance(s) • Gas Cooktop
Neighborhood
Public Transportation • Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl Second24.5 x 17.416666666
Flooring - Wood, Recessed Lighting, Lighting - Overhead, Archway
Dining Room
Lvl Second14.25 x 16.416666666
Flooring - Wood, Chair Rail, Recessed Lighting, Lighting - Pendant, Pocket Door, Tray Ceiling(s)
Kitchen
Lvl Second15.083333333 x 12
Flooring - Wood, Countertops - Stone/Granite/Solid, Kitchen Island, Recessed Lighting, Stainless Steel Appliances, Peninsula, Lighting - Pendant
Family Room
Lvl Second15.083333333 x 19.083333333
Ceiling Fan(s), Closet, Closet/Cabinets - Custom Built, Flooring - Wood, Recessed Lighting, Lighting - Overhead
Master Bedroom
Lvl Third13.083333333 x 19.666666666
Bathroom - Full, Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Wood, Recessed Lighting, Tray Ceiling(s)
Bedroom 2
Lvl Main,First13.75 x 16.583333333
Bedroom 3
Lvl Main,First13.666666666 x 15.916666666
Flooring - Wall to Wall Carpet, Lighting - Pendant, Decorative Molding
Bedroom 4
Lvl Third9.833333333 x 14.25
Ceiling Fan(s), Closet, Flooring - Wood, Lighting - Overhead
Bathroom 1
Lvl First5.25 x 8.166666666
Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Lighting - Sconce, Lighting - Pendant
Bathroom 2
Lvl SecondBathroom - Half, Flooring - Stone/Ceramic Tile, Lighting - Sconce, Lighting - Overhead, Pedestal Sink
Bathroom 3
Lvl Third15.416666666 x 16.25
Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Tub & Shower, Bathroom - With Shower Stall, Skylight, Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Marble, Countertops - Stone/Granite/Solid, Recessed Lighting, Lighting - Pendant
Property History
$2,500,000
Sep 8, 2026
MLS® 73573036
$2,500,000
Sep 8, 2026
MLS® 73573042
$2,700,000
Jul 1, 2026
MLS® 73533495
$2,700,000
Jul 1, 2026
MLS® 73532468
$2,700,000
Jun 10, 2026
MLS® 73533495
$2,700,000
Jun 9, 2026
MLS® 73532468
$3,100
Aug 15, 2025
MLS® 73413001
$3,100
Aug 3, 2025
MLS® 73413001
Listing Agent: Nancy Roth
Listing Office: Gibson Sotheby's International Realty
MLS® Number: 73573036
